JPS6212776B2 - - Google Patents
Info
- Publication number
- JPS6212776B2 JPS6212776B2 JP54164098A JP16409879A JPS6212776B2 JP S6212776 B2 JPS6212776 B2 JP S6212776B2 JP 54164098 A JP54164098 A JP 54164098A JP 16409879 A JP16409879 A JP 16409879A JP S6212776 B2 JPS6212776 B2 JP S6212776B2
- Authority
- JP
- Japan
- Prior art keywords
- methanol
- gas
- unsaturated aldehyde
- water
- tower
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 129
- 238000000034 method Methods 0.000 claims description 18
- 230000003647 oxidation Effects 0.000 claims description 9
- 238000007254 oxidation reaction Methods 0.000 claims description 9
- 230000003197 catalytic effect Effects 0.000 claims description 8
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 6
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 6
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 6
- 239000002994 raw material Substances 0.000 claims description 5
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 3
- 239000007789 gas Substances 0.000 description 59
- 150000001299 aldehydes Chemical class 0.000 description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 22
- 230000018044 dehydration Effects 0.000 description 22
- 238000006297 dehydration reaction Methods 0.000 description 22
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 11
- 238000010521 absorption reaction Methods 0.000 description 9
- 239000007795 chemical reaction product Substances 0.000 description 9
- 239000012071 phase Substances 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 8
- 238000010791 quenching Methods 0.000 description 8
- 230000000171 quenching effect Effects 0.000 description 8
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 229910002091 carbon monoxide Inorganic materials 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 239000002274 desiccant Substances 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000009834 vaporization Methods 0.000 description 2
- 230000008016 vaporization Effects 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- UBAZGMLMVVQSCD-UHFFFAOYSA-N carbon dioxide;molecular oxygen Chemical compound O=O.O=C=O UBAZGMLMVVQSCD-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000006709 oxidative esterification reaction Methods 0.000 description 1
- 239000012495 reaction gas Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/33—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties
- C07C45/34—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds
- C07C45/35—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds in propene or isobutene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/37—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of >C—O—functional groups to >C=O groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/783—Separation; Purification; Stabilisation; Use of additives by gas-liquid treatment, e.g. by gas-liquid absorption
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Gas Separation By Absorption (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16409879A JPS5687530A (en) | 1979-12-19 | 1979-12-19 | Dehydrating method of gas containing unsaturated aldehyde |
| US06/213,703 US4329513A (en) | 1979-12-19 | 1980-12-05 | Method for dehydration of unsaturated aldehyde-containing gas |
| GB8039692A GB2065650B (en) | 1979-12-19 | 1980-12-11 | Mehtod for dehydration of unsaturated aldehyde-containing gas |
| DE3047485A DE3047485C2 (de) | 1979-12-19 | 1980-12-17 | Verfahren zur Dehydratisierung eines Gases enthaltend Acrolein bzw. Methacrolein |
| SU803217952A SU1442065A3 (ru) | 1979-12-19 | 1980-12-17 | Способ осушки углеводородного газа |
| FR8026973A FR2471964A1 (fr) | 1979-12-19 | 1980-12-18 | Procede de deshydratation d'un gaz contenant un aldehyde insature et procede de recuperation d'un aldehyde insature ayant une faible teneur en eau |
| IT26798/80A IT1151467B (it) | 1979-12-19 | 1980-12-19 | Procedimento per la disidratazione di gas contenenti aldeidi insature |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16409879A JPS5687530A (en) | 1979-12-19 | 1979-12-19 | Dehydrating method of gas containing unsaturated aldehyde |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5687530A JPS5687530A (en) | 1981-07-16 |
| JPS6212776B2 true JPS6212776B2 (de) | 1987-03-20 |
Family
ID=15786720
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16409879A Granted JPS5687530A (en) | 1979-12-19 | 1979-12-19 | Dehydrating method of gas containing unsaturated aldehyde |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4329513A (de) |
| JP (1) | JPS5687530A (de) |
| DE (1) | DE3047485C2 (de) |
| FR (1) | FR2471964A1 (de) |
| GB (1) | GB2065650B (de) |
| IT (1) | IT1151467B (de) |
| SU (1) | SU1442065A3 (de) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69033068T2 (de) * | 1989-12-06 | 1999-08-19 | Nippon Catalytic Chem Ind | Verfahren zur Herstellung von Methacrolein und Methacrylsäure |
| SG71815A1 (en) * | 1997-07-08 | 2000-04-18 | Asahi Chemical Ind | Method of producing methyl methacrylate |
| TW201509522A (zh) | 2013-07-29 | 2015-03-16 | Rohm & Haas | 氧化酯化催化劑 |
| TW201509901A (zh) | 2013-07-29 | 2015-03-16 | Rohm & Haas | 氧化酯化方法 |
| SG11201703365VA (en) | 2014-10-31 | 2017-05-30 | Dow Global Technologies Llc | Process for in situ water removal from an oxidative esterification reaction using a coupled reactor-distillation system |
| WO2016069225A1 (en) | 2014-10-31 | 2016-05-06 | Rohm And Haas Company | Oxidative esterification process for making methyl methacrylate |
| JP2023544155A (ja) * | 2020-09-30 | 2023-10-20 | ゲノミウム，インコーポレイテッド | バイオアクロレイン及びバイオアクリル酸を生成するための発酵プロセス |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2514966A (en) * | 1948-01-09 | 1950-07-11 | Shell Dev | Refining and concentrating crude unsaturated aldehydes by extractive distillation |
| US2514967A (en) * | 1948-09-17 | 1950-07-11 | Shell Dev | Refining and concentrating crude unsaturated aldehydes |
| US2767216A (en) * | 1955-10-31 | 1956-10-16 | Shell Dev | Drying of acrolein by extractive separation with glycerol |
| JPS4823409B1 (de) * | 1970-03-04 | 1973-07-13 | ||
| JPS547768B2 (de) * | 1973-01-06 | 1979-04-10 |
-
1979
- 1979-12-19 JP JP16409879A patent/JPS5687530A/ja active Granted
-
1980
- 1980-12-05 US US06/213,703 patent/US4329513A/en not_active Expired - Lifetime
- 1980-12-11 GB GB8039692A patent/GB2065650B/en not_active Expired
- 1980-12-17 DE DE3047485A patent/DE3047485C2/de not_active Expired
- 1980-12-17 SU SU803217952A patent/SU1442065A3/ru active
- 1980-12-18 FR FR8026973A patent/FR2471964A1/fr active Granted
- 1980-12-19 IT IT26798/80A patent/IT1151467B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| US4329513A (en) | 1982-05-11 |
| FR2471964A1 (fr) | 1981-06-26 |
| DE3047485A1 (de) | 1981-09-24 |
| GB2065650A (en) | 1981-07-01 |
| DE3047485C2 (de) | 1983-05-26 |
| IT1151467B (it) | 1986-12-17 |
| GB2065650B (en) | 1983-12-21 |
| IT8026798A0 (it) | 1980-12-19 |
| SU1442065A3 (ru) | 1988-11-30 |
| FR2471964B1 (de) | 1983-01-28 |
| JPS5687530A (en) | 1981-07-16 |
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